KFS CEO Fitzgerald adds to holdings via 197-share ESPP purchase

Rhea-AI Filing Summary

Kingsway Financial Services Inc. (KFS) President and CEO John Taylor Maloney Fitzgerald reported acquiring 197 shares of common stock on November 17, 2025 through a purchase coded “P” under the Kingsway America Inc. Employee Share Purchase Plan (ESPP) at $12.70 per share.

After this transaction, he beneficially owns 1,489,147 shares of common stock directly, plus 34,100 shares held in each of three separate trusts. The directly held amount includes 400,000 shares of restricted stock granted on March 31, 2021. Under the ESPP, eligible employees can contribute up to 5% of adjusted salary, and the company matches 100% of that contribution once a 12‑month service requirement is met.

Insider Trade Summary

Net Buyer: 197 shares ($2,502)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 197 shs ($3K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	197	$12.70	$3K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,489,147 shares (Direct); Common Stock — 34,100 shares (Indirect, Trust-GEF)

Footnotes (1)

1. The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker. Includes 400,000 shares of restricted stock granted on March 31, 2021.

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Fitzgerald John Taylor Maloney

(Last) (First) (Middle)

10 S. RIVERSIDE PLAZA

SUITE 1520

(Street)

CHICAGO IL 60606

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
KINGSWAY FINANCIAL SERVICES INC [ KFS ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President and CEO

3. Date of Earliest Transaction (Month/Day/Year)
11/17/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	11/17/2025		P		197(1)	A	$12.7	1,489,147(2)	D
Common Stock								34,100	I	Trust-GEF
Common Stock								34,100	I	Trust-LTF
Common Stock								34,100	I	Trust-MPF

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

2. Includes 400,000 shares of restricted stock granted on March 31, 2021.

	/s/ Robert E. Buckner II, attorney-in-fact for John Taylor Maloney Fitzgerald	11/19/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What did KFS report in this Form 4 filing?

The filing reports that John Taylor Maloney Fitzgerald, President and CEO of Kingsway Financial Services Inc. (KFS), acquired 197 shares of KFS common stock on November 17, 2025 through a purchase transaction.

At what price were the new KFS shares acquired by the CEO?

The 197 shares of KFS common stock were acquired at a price of $12.70 per share in the reported transaction.

How many KFS shares does the CEO beneficially own after this transaction?

Following the transaction, the CEO beneficially owns 1,489,147 shares of KFS common stock directly, plus 34,100 shares held in each of three separate trusts.

What is the Kingsway America Inc. Employee Share Purchase Plan (ESPP)?

The ESPP allows eligible employees to contribute up to 5% of adjusted salary each payroll period. After 12 months of employment with Kingsway America Inc. and its subsidiaries, the company makes a 100% matching contribution, and both contributions are used to buy KFS shares on the open market.

How are shares acquired under the KFS ESPP actually purchased?

Under the ESPP, employee and company matching contributions are used to purchase shares of Kingsway Financial Services Inc. on the open market, as soon as administratively practicable, through a duly registered stockbroker acting as administrator.

Does the CEO’s beneficial ownership include restricted stock in KFS?

Yes. The beneficial ownership figure includes 400,000 shares of restricted stock that were granted on March 31, 2021.